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#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/11/7201153.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7201153
loop_
_publ_author_name
'Nauha, Elisa'
'Saxell, Heidi'
'Nissinen, Maija'
'Kolehmainen, Erkki'
'Schäfer, Ansgar'
'Schlecker, Rainer'
_publ_section_title
;
 Polymorphism and versatile solvate formation of thiophanate-methyl
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2536
_journal_paper_doi               10.1039/b905511h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C12 H14 N4 O4 S2'
_chemical_formula_sum            'C12 H14 N4 O4 S2'
_chemical_formula_weight         342.39
_chemical_name_common            thiophanate-methyl
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 132.593(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7149(5)
_cell_length_b                   11.8405(5)
_cell_length_c                   15.6861(6)
_cell_measurement_temperature    103(2)
_cell_volume                     1465.07(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9506
_diffrn_reflns_theta_full        54.86
_diffrn_reflns_theta_max         54.86
_diffrn_reflns_theta_min         5.35
_exptl_absorpt_coefficient_mu    3.532
_exptl_absorpt_correction_T_max  0.5385
_exptl_absorpt_correction_T_min  0.5385
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0067(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         1744
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0483P)²+3.0780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1199
_reflns_number_gt                1620
_reflns_number_total             1744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905511h.txt
_cod_data_source_block           TM_formI
_cod_original_cell_volume        1465.06(11)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7201153
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.05783(12) 0.97077(8) 0.38905(8) 0.0222(4) Uani 1 1 d . . .
S2 S 0.81503(12) 0.86570(8) 0.74422(8) 0.0252(4) Uani 1 1 d . . .
O1 O 0.0845(3) 0.6392(2) 0.5512(2) 0.0222(7) Uani 1 1 d . . .
O2 O -0.1068(3) 0.7291(2) 0.5459(2) 0.0256(7) Uani 1 1 d . . .
O3 O 0.3561(3) 1.0053(2) 0.6746(2) 0.0268(7) Uani 1 1 d . . .
O4 O 0.5598(3) 1.0563(2) 0.8618(2) 0.0251(7) Uani 1 1 d . . .
N1 N -0.0054(4) 0.8212(3) 0.4813(3) 0.0195(8) Uani 1 1 d D . .
H1 H -0.062(4) 0.879(2) 0.479(3) 0.023 Uiso 1 1 d D . .
N2 N 0.1878(4) 0.7649(3) 0.4684(3) 0.0180(8) Uani 1 1 d D . .
H2 H 0.189(5) 0.696(2) 0.495(3) 0.022 Uiso 1 1 d D . .
N3 N 0.4772(4) 0.8990(3) 0.5933(3) 0.0198(8) Uani 1 1 d D . .
H3 H 0.392(4) 0.933(3) 0.581(3) 0.024 Uiso 1 1 d D . .
N4 N 0.6380(4) 0.9786(3) 0.7753(3) 0.0213(8) Uani 1 1 d D . .
H4 H 0.744(3) 0.992(3) 0.842(2) 0.026 Uiso 1 1 d D . .
C1 C -0.1115(6) 0.6312(3) 0.6000(4) 0.0288(10) Uani 1 1 d . . .
H1A H -0.1624 0.5672 0.5462 0.043 Uiso 1 1 calc R . .
H1B H -0.1793 0.6490 0.6192 0.043 Uiso 1 1 calc R . .
H1C H 0.0042 0.6117 0.6708 0.043 Uiso 1 1 calc R . .
C2 C -0.0018(5) 0.7206(4) 0.5285(3) 0.0213(10) Uani 1 1 d . . .
C3 C 0.0833(5) 0.8455(3) 0.4486(3) 0.0194(9) Uani 1 1 d . . .
C4 C 0.2815(5) 0.7729(3) 0.4333(3) 0.0197(9) Uani 1 1 d . . .
C5 C 0.2291(5) 0.7100(3) 0.3393(3) 0.0231(10) Uani 1 1 d . . .
H5 H 0.1275 0.6671 0.2957 0.028 Uiso 1 1 calc R . .
C6 C 0.3235(5) 0.7092(3) 0.3086(3) 0.0251(10) Uani 1 1 d . . .
H6 H 0.2867 0.6664 0.2438 0.030 Uiso 1 1 calc R . .
C7 C 0.4733(5) 0.7718(3) 0.3737(3) 0.0237(10) Uani 1 1 d . . .
H7 H 0.5398 0.7705 0.3539 0.028 Uiso 1 1 calc R . .
C8 C 0.5251(5) 0.8356(3) 0.4668(3) 0.0215(9) Uani 1 1 d . . .
H8 H 0.6257 0.8794 0.5096 0.026 Uiso 1 1 calc R . .
C9 C 0.4309(5) 0.8361(3) 0.4984(3) 0.0196(9) Uani 1 1 d . . .
C10 C 0.6334(5) 0.9148(3) 0.6974(3) 0.0202(9) Uani 1 1 d . . .
C11 C 0.5039(5) 1.0131(3) 0.7618(3) 0.0216(9) Uani 1 1 d . . .
C12 C 0.4236(5) 1.0903(4) 0.8565(4) 0.0275(10) Uani 1 1 d . . .
H12A H 0.3682 1.1583 0.8086 0.041 Uiso 1 1 calc R . .
H12B H 0.4709 1.1063 0.9349 0.041 Uiso 1 1 calc R . .
H12C H 0.3403 1.0292 0.8225 0.041 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C1 115.3(3) . . ?
C11 O4 C12 113.5(3) . . ?
C3 N1 C2 126.7(3) . . ?
C3 N1 H1 116(3) . . ?
C2 N1 H1 117(3) . . ?
C3 N2 C4 123.7(3) . . ?
C3 N2 H2 120(2) . . ?
C4 N2 H2 115(2) . . ?
C10 N3 C9 127.7(3) . . ?
C10 N3 H3 117(3) . . ?
C9 N3 H3 116(3) . . ?
C11 N4 C10 127.6(3) . . ?
C11 N4 H4 120(3) . . ?
C10 N4 H4 112(3) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 125.7(4) . . ?
O1 C2 N1 125.5(3) . . ?
O2 C2 N1 108.8(3) . . ?
N2 C3 N1 116.3(3) . . ?
N2 C3 S1 123.8(3) . . ?
N1 C3 S1 119.9(3) . . ?
C5 C4 C9 120.2(3) . . ?
C5 C4 N2 119.1(3) . . ?
C9 C4 N2 120.5(3) . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 119.1(3) . . ?
C8 C9 N3 123.5(3) . . ?
C4 C9 N3 117.4(3) . . ?
N3 C10 N4 114.4(3) . . ?
N3 C10 S2 128.0(3) . . ?
N4 C10 S2 117.6(3) . . ?
O3 C11 O4 123.9(4) . . ?
O3 C11 N4 126.1(3) . . ?
O4 C11 N4 110.0(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.674(4) . ?
S2 C10 1.652(4) . ?
O1 C2 1.210(5) . ?
O2 C2 1.329(5) . ?
O2 C1 1.457(5) . ?
O3 C11 1.207(5) . ?
O4 C11 1.345(5) . ?
O4 C12 1.462(5) . ?
N1 C3 1.382(5) . ?
N1 C2 1.389(5) . ?
N1 H1 0.900(19) . ?
N2 C3 1.339(5) . ?
N2 C4 1.437(5) . ?
N2 H2 0.903(19) . ?
N3 C10 1.343(5) . ?
N3 C9 1.420(5) . ?
N3 H3 0.896(19) . ?
N4 C11 1.365(5) . ?
N4 C10 1.409(5) . ?
N4 H4 0.90(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.387(5) . ?
C4 C9 1.397(5) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(5) . ?
C8 H8 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.900(19) 2.70(3) 3.473(3) 144(3) 3_576
N2 H2 O1 0.903(19) 1.97(3) 2.660(4) 132(3) .
N2 H2 O4 0.903(19) 2.62(3) 3.280(4) 131(3) 2_646
N3 H3 O3 0.896(19) 1.94(3) 2.671(4) 137(3) .
N3 H3 S1 0.896(19) 2.74(3) 3.419(3) 134(3) .
N4 H4 O1 0.90(2) 2.25(3) 2.985(4) 139(3) 2_656
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O2 C2 O1 1.7(5) . . . . ?
C1 O2 C2 N1 -177.5(3) . . . . ?
C3 N1 C2 O1 2.2(6) . . . . ?
C3 N1 C2 O2 -178.6(3) . . . . ?
C4 N2 C3 N1 175.9(3) . . . . ?
C4 N2 C3 S1 -4.6(5) . . . . ?
C2 N1 C3 N2 -2.5(5) . . . . ?
C2 N1 C3 S1 178.0(3) . . . . ?
C3 N2 C4 C5 -105.5(4) . . . . ?
C3 N2 C4 C9 79.6(5) . . . . ?
C9 C4 C5 C6 -0.2(6) . . . . ?
N2 C4 C5 C6 -175.1(3) . . . . ?
C4 C5 C6 C7 0.4(6) . . . . ?
C5 C6 C7 C8 -1.1(6) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C7 C8 C9 C4 -1.2(5) . . . . ?
C7 C8 C9 N3 179.6(3) . . . . ?
C5 C4 C9 C8 0.5(5) . . . . ?
N2 C4 C9 C8 175.4(3) . . . . ?
C5 C4 C9 N3 179.8(3) . . . . ?
N2 C4 C9 N3 -5.3(5) . . . . ?
C10 N3 C9 C8 -39.2(6) . . . . ?
C10 N3 C9 C4 141.6(4) . . . . ?
C9 N3 C10 N4 -178.0(3) . . . . ?
C9 N3 C10 S2 -0.1(6) . . . . ?
C11 N4 C10 N3 8.4(5) . . . . ?
C11 N4 C10 S2 -169.7(3) . . . . ?
C12 O4 C11 O3 1.8(5) . . . . ?
C12 O4 C11 N4 -177.1(3) . . . . ?
C10 N4 C11 O3 -8.7(6) . . . . ?
C10 N4 C11 O4 170.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2297683
